WO2009088456A2 - Impact-resistant polyurethanes - Google Patents

Impact-resistant polyurethanes Download PDF

Info

Publication number
WO2009088456A2
WO2009088456A2 PCT/US2008/014069 US2008014069W WO2009088456A2 WO 2009088456 A2 WO2009088456 A2 WO 2009088456A2 US 2008014069 W US2008014069 W US 2008014069W WO 2009088456 A2 WO2009088456 A2 WO 2009088456A2
Authority
WO
WIPO (PCT)
Prior art keywords
molecular weight
prepolymer
polyol
curing agent
diol
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/US2008/014069
Other languages
English (en)
French (fr)
Other versions
WO2009088456A3 (en
Inventor
Richard M. Gerkin
Edmond J Derderian
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
PolyPlexx LLC
Original Assignee
PolyPlexx LLC
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from US11/968,622 external-priority patent/US20090171059A1/en
Application filed by PolyPlexx LLC filed Critical PolyPlexx LLC
Priority to JP2010541435A priority Critical patent/JP5638959B2/ja
Priority to EP08869399A priority patent/EP2227500B1/en
Priority to ES08869399T priority patent/ES2380766T3/es
Priority to AT08869399T priority patent/ATE544796T1/de
Priority to MX2010007379A priority patent/MX2010007379A/es
Publication of WO2009088456A2 publication Critical patent/WO2009088456A2/en
Publication of WO2009088456A3 publication Critical patent/WO2009088456A3/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
    • C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
    • C08G18/758—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing two or more cycloaliphatic rings
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
    • C08G18/12—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step using two or more compounds having active hydrogen in the first polymerisation step
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
    • C08G18/3203—Polyhydroxy compounds
    • C08G18/3212—Polyhydroxy compounds containing cycloaliphatic groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
    • C08G18/3203—Polyhydroxy compounds
    • C08G18/3218—Polyhydroxy compounds containing cyclic groups having at least one oxygen atom in the ring
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
    • C08G18/4266—Polycondensates having carboxylic or carbonic ester groups in the main chain prepared from hydroxycarboxylic acids and/or lactones
    • C08G18/4269—Lactones
    • C08G18/4277—Caprolactone and/or substituted caprolactone
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/48—Polyethers
    • C08G18/4854—Polyethers containing oxyalkylene groups having four carbon atoms in the alkylene group
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/48—Polyethers
    • C08G18/50—Polyethers having heteroatoms other than oxygen
    • C08G18/5021—Polyethers having heteroatoms other than oxygen having nitrogen
    • C08G18/5024—Polyethers having heteroatoms other than oxygen having nitrogen containing primary and/or secondary amino groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2120/00—Compositions for reaction injection moulding processes

Definitions

  • Polyurethanes are a known class of materials that have found extensive commercial application because of their excellent physical properties. These polymers are suitable for molding, spraying, and coating products where tensile strength, toughness, and impact resistance are required.
  • a one-shot system whereby the polyisocyanate and active hydrogen compounds are converted to the final product in a single reaction step.
  • an intermediate product usually called a prepolymer, is formed first by reacting a stoichiometric excess of a polyisocyanate with an active hydrogen compound, and the prepolymer is subsequently converted to the final polymer in a second reaction involving a further active hydrogen compound, commonly called a chain extender or curing agent.
  • the polyurethane is the reaction product of: 1) A prepolymer made by reacting a cycloaliphatic polyisocyanate with a primary amine-terminated polyether diamine of 2000 to about 2500 molecular weight to give a prepolymer free-NCO content of >18%, more preferably from about 18% to 23%, and 2) A polyol selected from the group consisting of (a) a polyester polyol triol with a molecular weight of between about 540 and 900, or (b) a polyether glycol with a molecular weight of between about 650 and 2000, or (c) a polyester polyol diol with a molecular weight of up to 2,000, and 3) A curing agent selected from the group consisting of (a) dianhydrohexitol or (b) aromatic diamine, or (c) cyclohexanedimethanol or (d) aromatic ring-containing diols.
  • the curing agent should be essentially free of, and more preferably free of, isocyanate reactive groups other than the aforementioned amine or hydroxyl groups, respectively.
  • Example 1 Prepolymer 12-86-1 160.Og (1.219 eq.) of lsocyanate 1 was added to a reaction flask equipped with a nitrogen inlet, stirrer, dropping funnel, heating mantle and thermocouple. The sample was placed under nitrogen and heated to 80 0 C, with stirring. 96.24g (0.0982 eq.) of Amine-terminated polyether 1 , was placed in the dropping funnel and added to the isocyanate over a period of 20 minutes. The temperature rose to 86.5°C and the reaction was held at that temperature for 30 min. after the polyether was added. The prepolymer was transferred to a storage container under nitrogen and placed in an oven at 70 to 80 0 C for about 16 hrs. Theoretical free-NCO of this prepolymer was 18.38%, actual was 18.32%, and equivalent weight was 229.26.
  • Example 20 Polymer, 70% Hard Segment 42-12-1

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Polyurethanes Or Polyureas (AREA)
PCT/US2008/014069 2008-01-02 2008-12-26 Impact-resistant polyurethanes Ceased WO2009088456A2 (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
JP2010541435A JP5638959B2 (ja) 2008-01-02 2008-12-26 耐衝撃性ポリウレタン
EP08869399A EP2227500B1 (en) 2008-01-02 2008-12-26 Impact-resistant polyurethanes
ES08869399T ES2380766T3 (es) 2008-01-02 2008-12-26 Poliuretanos resistentes al impacto
AT08869399T ATE544796T1 (de) 2008-01-02 2008-12-26 Schlagfeste polyurethane
MX2010007379A MX2010007379A (es) 2008-01-02 2008-12-26 Poliuretanos resistentes al impacto.

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US11/968,622 US20090171059A1 (en) 2008-01-02 2008-01-02 Impact-Resistant Polyurethane
US11/968,622 2008-01-02
US11/971,843 2008-01-09
US11/971,843 US8178644B2 (en) 2008-01-02 2008-01-09 Impact-resistant polyurethane

Publications (2)

Publication Number Publication Date
WO2009088456A2 true WO2009088456A2 (en) 2009-07-16
WO2009088456A3 WO2009088456A3 (en) 2009-09-11

Family

ID=40791185

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2008/014069 Ceased WO2009088456A2 (en) 2008-01-02 2008-12-26 Impact-resistant polyurethanes

Country Status (8)

Country Link
US (1) US8178644B2 (enExample)
EP (1) EP2227500B1 (enExample)
JP (1) JP5638959B2 (enExample)
KR (1) KR101598642B1 (enExample)
AT (1) ATE544796T1 (enExample)
ES (1) ES2380766T3 (enExample)
MX (1) MX2010007379A (enExample)
WO (1) WO2009088456A2 (enExample)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2011144216A (ja) * 2010-01-12 2011-07-28 Sumitomo Chemical Co Ltd 光学フィルム及び光学フィルムの製造方法
KR20160149244A (ko) 2014-07-08 2016-12-27 미쯔이가가꾸가부시끼가이샤 광학 재료용 중합성 조성물 및 그 용도
WO2018079518A1 (ja) 2016-10-25 2018-05-03 三井化学株式会社 光学材料用重合性組成物、該組成物から得られた光学材料及びその製造方法
US11718765B2 (en) 2017-10-27 2023-08-08 Roquette Freres Polyurethane coating comprising isosorbide

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US8372939B1 (en) * 2009-08-17 2013-02-12 Polyplexx, Llc Transparent polyurethanes
WO2012083149A1 (en) * 2010-12-17 2012-06-21 Cargill, Incorporated Reaction product from the dehydration of sorbitol
WO2012083146A1 (en) * 2010-12-17 2012-06-21 Cargill, Incorporated Reaction product from the co-dehydration of a sugar alcohol and a polyol
WO2013139704A1 (de) * 2012-03-20 2013-09-26 Bayer Intellectual Property Gmbh Lagerstabile polyurethan-prepregs und daraus hergestellte faserverbundbauteile
CN105246952A (zh) * 2013-04-19 2016-01-13 科思创德国股份公司 聚氨酯预浸料和由其制造的纤维复合元件
DE102013216751A1 (de) * 2013-08-23 2015-02-26 Evonik Industries Ag Modifizierte Alkoxylierungsprodukte, die Alkoxysilylgruppen aufweisen und Urethangruppen enthalten und deren Verwendung
US9500445B2 (en) * 2013-09-10 2016-11-22 The United States Of America As Represented By The Secretary Of The Army Multi-layer matrix composite having improved energy absorption, dissipation and shock wave mitigation capabilities
FR3027024B1 (fr) * 2014-10-09 2016-11-25 Roquette Freres Procede de preparation de granules de polyurethane thermoplastique
US20180016385A1 (en) * 2015-04-01 2018-01-18 Samyang Corporation Polyurethane, and its preparation method and use
US11059746B2 (en) 2015-08-10 2021-07-13 America as represented by the Secretary of the Army Thermoplastic cycloaliphatic polyamide matrix resins for next-generation energy absorbing applications
EP3603774A4 (en) 2017-03-24 2020-12-09 Toray Industries, Inc. FILTER MEDIUM AND BAG FILTER
CN107857861A (zh) * 2017-10-19 2018-03-30 哈尔滨师范大学 一种非离子表面活性剂及其制备方法
CA3088735A1 (en) * 2018-01-25 2019-08-01 Novol, Inc. Sorbitol-based crosslinked optical polymers
JP7012821B2 (ja) * 2018-03-16 2022-01-28 三井化学株式会社 光学材料用重合性組成物、光学材料用重合性組成物の製造方法および光学物品の製造方法
JP7268015B2 (ja) * 2018-05-30 2023-05-02 三井化学株式会社 光学用ポリウレタン樹脂、ディスプレイパネル用カバー板、アイウェア材料、アイウェアレンズ、アイウェアフレーム、自動車内外装材用部品、および、光学用ポリウレタン樹脂の製造方法
CN110343228B (zh) * 2019-07-25 2021-08-06 江苏瑞文新材料科技有限公司 一种电缆护套用耐水快速修补料及其应用
CN113773470A (zh) * 2021-09-16 2021-12-10 株洲时代新材料科技股份有限公司 一种耐老化的聚氨酯材料、制备方法和应用

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Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2011144216A (ja) * 2010-01-12 2011-07-28 Sumitomo Chemical Co Ltd 光学フィルム及び光学フィルムの製造方法
KR20160149244A (ko) 2014-07-08 2016-12-27 미쯔이가가꾸가부시끼가이샤 광학 재료용 중합성 조성물 및 그 용도
US10308756B2 (en) 2014-07-08 2019-06-04 Mitsui Chemicals, Inc. Polymerizable composition for optical material and use thereof
WO2018079518A1 (ja) 2016-10-25 2018-05-03 三井化学株式会社 光学材料用重合性組成物、該組成物から得られた光学材料及びその製造方法
KR20190039259A (ko) 2016-10-25 2019-04-10 미쯔이가가꾸가부시끼가이샤 광학 재료용 중합성 조성물, 해당 조성물로부터 얻어진 광학 재료 및 그 제조 방법
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US11180602B2 (en) 2016-10-25 2021-11-23 Mitsui Chemicals, Inc. Polymerizable composition for optical material, optical material obtained from composition, method of producing same
US11718765B2 (en) 2017-10-27 2023-08-08 Roquette Freres Polyurethane coating comprising isosorbide

Also Published As

Publication number Publication date
ES2380766T3 (es) 2012-05-18
WO2009088456A3 (en) 2009-09-11
MX2010007379A (es) 2010-12-07
JP2011508822A (ja) 2011-03-17
KR101598642B1 (ko) 2016-02-29
US20090171060A1 (en) 2009-07-02
US8178644B2 (en) 2012-05-15
EP2227500B1 (en) 2012-02-08
KR20100115751A (ko) 2010-10-28
EP2227500A2 (en) 2010-09-15
ATE544796T1 (de) 2012-02-15
JP5638959B2 (ja) 2014-12-10

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